Total Synthesis of Baccatin III and Taxol

1996/01/01 by Samuel J. Danishefsky, John J. Masters, Wendy B. Young +9 · 12 citations
Medicine · Chemistry · #Cancer Treatment and Pharmacology #Synthetic Organic Chemistry Methods #Chemical synthesis and alkaloids

paper · doi:10.1021/ja952692a

openalex publication_date 1996/01/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/26

Abstract

An intramolecular Heck reaction ( 90 → 91 ) serves as the key step in the total synthesis of the titled compounds. The synthetic route is based on utilizing the Wieland−Miescher ketone ( 5 ) as a matrix to provide the C and D rings of the targets and to provide functionality implements for joining this sector to an A ring precursor ( 6 ). Catalytically induced enantiotopic control and early emplacement of the oxetane are other features of the route.

Citations

• First total synthesis of taxol. 2. Completion of the C and D rings
• Organoselenium chemistry. A facile one-step synthesis of alkyl aryl selenides from alcohols
• First total synthesis of taxol. 1. Functionalization of the B ring

Cited by

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• Enantioselective Total Synthesis of (−)-Taxol
• A Formal Total Synthesis of Taxol Aided by an Automated Synthesizer
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• The IntramolecularHeck Reaction
• Terpenoids
• A brief overview of classical natural product drug synthesis and bioactivity
• Inspirations, Discoveries, and Future Perspectives in Total Synthesis
• Wieland–Miescher ketone [wikipedia]